Holiday rentals near Winter Island Maritime Park

We found 326 holiday rentals — enter your dates for availability

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August 2025

September 2025

If you are looking to stay near Winter Island Maritime Park, take a look at holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Winter Island Maritime Park

Showing deals for:21 Nov - 28 Nov

Exceptional

(10 reviews)

NEW 2BR Historic Marblehead Home+Minutes to Beach

Marblehead, MA

8% off

AU$496 nightly

Includes taxes & fees

Exceptional

(69 reviews)

3 bedroom condo nestled in Historic fishing village - dog friendly

Swampscott, MA

21% off

AU$522 nightly

Includes taxes & fees

Rental is for entire house, including deck and 5 bedrooms

Exceptional

(92 reviews)

Walkable to Everything Great about Marblehead! Perfect for multiple families -12

Marblehead, MA

8% off

AU$1,072 nightly

Includes taxes & fees

Exceptional

(62 reviews)

Historic Federal Period brick mansion on fabled Chestnut Street, Salem, MA

Salem, MA

8% off

AU$2,343 nightly

Includes taxes & fees

Essex River is one of the main waterways in what is called The Great Marsh

Exceptional

(26 reviews)

❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

Essex, MA

21% off

AU$771 nightly

Includes taxes & fees

Exceptional

(60 reviews)

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Marblehead, MA

8% off

AU$319 nightly

Includes taxes & fees

Exceptional

(122 reviews)

Modern Condo in Historic Marblehead, Walk everywhere, Parking, A/C, Deck & Grill

Marblehead, MA

8% off

AU$905 nightly

Includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Winter Island Maritime Park

Stunning Beach Cottage just steps from Marblehead Harbor and Town

Sleeps 6 · 2 bedrooms · 1 bathroom

Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown

Sleeps 2 · 1 bedroom · 1 bathroom

Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

Sleeps 14 · 6 bedrooms · 3+ bathrooms

NEW 1BR on Salem Common l Steps to Witch Museum and Downtown l Fenced in Yard

Sleeps 4 · 1 bedroom · 1 bathroom

Top rated rentals - Winter Island Maritime Park

Premier Host

Highly-Recommended Getaway in Marblehead

Conveniently located and well maintained, this cottage was the perfect lodging for my solo vacation to the region. The well-stocked kitchen, spacious bathroom, and wood-burning stove (very easy to start) were just some of its many amenities. The one-page list of house rules and instructions was clear and easy to follow, which I greatly appreciated. And it was apparent that the property had been thoroughly cleaned and prepared for my arrival. Overall, I couldn’t have been more pleased with my stay, and I will certainly keep this gem in mind for future trips. Thank you, property owners!

Heather M.

Stayed Mar 2021

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Enjoy full kitchens, laundry, pools, gardens and more
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